US11528924B2 - Alcoholic beverage substitutes - Google Patents

Alcoholic beverage substitutes Download PDF

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US11528924B2
US11528924B2 US15/534,121 US201515534121A US11528924B2 US 11528924 B2 US11528924 B2 US 11528924B2 US 201515534121 A US201515534121 A US 201515534121A US 11528924 B2 US11528924 B2 US 11528924B2
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substitute
less
beverage
alcohol
alcoholic
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US20170360067A1 (en
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Ezekiel Golan
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Clearmind Medicine Inc
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Clearmind Medicine Inc
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/38—Other non-alcoholic beverages
    • A23L2/382—Other non-alcoholic beverages fermented
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/32—Alcohol-abuse
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12G—WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES; PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H
    • C12G3/00—Preparation of other alcoholic beverages
    • C12G3/04—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs
    • C12G3/06—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs with flavouring ingredients
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12G—WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES; PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H
    • C12G3/00—Preparation of other alcoholic beverages
    • C12G3/08—Preparation of other alcoholic beverages by methods for altering the composition of fermented solutions or alcoholic beverages not provided for in groups C12G3/02 - C12G3/07

Definitions

  • the present invention in some embodiments thereof, relates to alcoholic beverage substitutes.
  • Alcohol consumption presents a growing problem worldwide, which some believe may have already overtaken tobacco in terms of overall health and social care costs. Excessive and/or prolonged alcohol consumption may have some undesired physiological and psychological including short-term effects such as gastric irritation, anxiety disorders and other excitable states, and longer-term effects such as cirrhosis, cardiomyopathy and dementia. Alcohol consumption may lead to intoxication, which, in turn, can have serious consequences such as accidents and uncontrolled violent behavior with subsequent medical complications.
  • the toxic element in alcohol is ethanol, a two-carbon chain alcohol that has a complex pharmacology.
  • the sedative, ataxic and eventually terminal anaesthetic actions of ethanol are thought to be mediated by interactions with primary amino acid ionotropic receptors, especially GABA A and glutamate.
  • Ethanol is known to act as a GABA A agonist, and hence increases inhibition of central GABA receptors, and as antagonist of the NMDA type of glutamate receptors, and hence reduces excitation in the central nervous system.
  • the pleasurable effects associated with alcohol consumption are attributed, at least in part, to these interactions, but are assumed to also involve interactions with endogenous opioids, dopamine and other amine systems.
  • Aspects of alcohol toxicity may reflect specific interactions, e.g., the nausea is in part due to agonist actions at the 5HT3 receptor leading to vagal nerve stimulation.
  • alcohol is consumed by drinking, usually over a few hours.
  • alcohol is provided as relatively dilute solution, wines are stronger and spirits contain the maximum alcohol concentration that can be obtained by simple distillation.
  • the “safer alcohol” approach which utilizes drugs that act in a similar way to alcohol but are free of some of its immediate adverse effects, such as, for example, gastric irritation, and do not produce the longer-term effects such as cirrhosis, cardiomyopathy and dementia.
  • the three main drug alternatives to alcohol that have been applied for alcohol withdrawal and treatment of anxiety disorders and other excitable states associated with excessive alcohol consumption include (i) Clomethiazole, a sedative hypnotic drug that was developed for sleep induction; (ii) benzodiazepine; and (iii) gammahydroxybutytrate (GHB), also used as an anaesthetic agent. All these drugs had limited use as treatment alternatives due to development of dependence thereon, and/or abuse thereof, and further since drinking alcohol on top of each of them could lead to excessive sedation and intoxication and potentially terminal coma.
  • GABA A receptor is one of the preferred receptor targets for an alcohol substitute.
  • Many GABA A receptor subunits ( ⁇ 1 , ⁇ 2 , ⁇ 2 , ⁇ 3 , ⁇ 2 and ⁇ ) have been shown to be involved in one or more aspects of ethanol behavioural sensitivity.
  • GABA A benzodiazepine receptor see, for example, Nutt and Malizia, 2001
  • PAs partial agonists of the GABA A receptor benzodiazepine site
  • PAs such as bretazenil show little sedation even in overdose, and few signs of dependence or withdrawal in animals have been reported. Moreover, they seem to have low to zero abuse propensity and have the additional safety benefit over alcohol, that an overdose can be instantly reversed by administering an antagonist such as, for example, flumazenil.
  • the dopamine D3 receptor subtype is a known target of anti-psychotics, and shows a high abundance in brain regions associated with emotional and cognitive functions. Compounds derived from 2-aminoindan have been shown to selectively bind to the dopamine D3 receptor.
  • U.S. Pat. No. 5,708,018 discloses some 2-aminoindan derivatives, and hypothesizes that these 2-aminoindan derivatives may be useful in treating CNS disorders associated with dopamine D3 receptor, such as mania, depression, drug abuse and addiction, anxiety disorders, and sleep disorders.
  • the present invention discloses alcoholic beverage substitutes, comprising a derivative of 2-aminoindan, as described herein.
  • the alcoholic beverage substitutes disclosed herein impart features such as psychotropic effect, palatability and pleasure that are attributed to alcoholic beverage, while avoiding the harmful effects associated with alcohol consumption.
  • the 2-aminoindan derivatives utilized in embodiments of the present invention are characterized as:
  • each of R 1 and R 2 is independently selected from the group consisting of H, (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, (C 3 -C 8 )cycloalkyl, aryl, heteroaryl, heteroalicyclic, —O(C 1 -C 8 )alkyl, OH, —OSO 2 CF 3 , —OSO 2 —(C 1 -C 8 )alkyl, —SOR 5 , —CO 2 R 5 , —CONR 5 R 6 , —COR 5 , —CF 3 , CN, —SR 5 , —SO 2 NR 5 R 6 , —SO 2 R 5 , —OCO—(C 1 -C 8 )alkyl, —NCO—(C 1 -C 8 )alkyl, —CH 2 O—(C 1 -C 8 )al
  • each of R 3 and R 4 is independently selected from the group consisting of H, (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, (C 3 -C 8 ) cycloalkyl, and —(CH 2 ) p -thienyl, wherein p is 1, 2, 3, or 4, or alternatively, R 3 and R 4 are joined together to form a heterocylic ring (heteroalicyclic or heteroaryl) containing the nitrogen atom to which they are attached; and
  • each of R 5 and R 6 is independently selected from the group consisting of H, (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 3 -C 8 )cycloalkyl and aryl;
  • each of R 1 and R 2 is independently selected from the group consisting of H, (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, (C 3 -C 8 )cycloalkyl, aryl, —OCH 3 , OH, —OSO 2 CF 3 , —OSO 2 CH 3 , —SOR 5 , —CO 2 R 5 , —CONR 5 R 6 , —COR 5 , —CF 3 , —CN, —SR 5 , —SO 2 NR 5 R 6 , —SO 2 R 5 , —CH 2 —OH, halogen, phthalimidyl, thiophenyl, pyrrolyl, pyrrolinyl, and oxazolyl, or, alternatively, R 1 and R 2 together with two or more of the pheny
  • R 3 and R 4 are joined together to form a heterocylic ring containing 4 to 8 carbon atoms with the nitrogen atom to which they are attached;
  • each of R 5 and R 6 is independently selected from the group consisting of H, (C 1 -C 8 ) alkyl, (C 2 -C 8 ) alkenyl, and (C 3 -C 8 ) cycloalkyl.
  • At least one of R 3 and R 4 is H.
  • each of R 1 and R 2 is H, —OCH 3 , or —OSO 2 CF 3 , or R 1 and R 2 together with two or more of the phenyl carbon atom form a —O(CH 2 ) m O— ring, wherein m is 1 or 2.
  • R 3 or R 4 is propyl
  • the compound is selected from:
  • the base liquid is a beverage selected from fruit juice, fruit syrup, concentrate or nectar from fruits jello, vegetable juice, a plant material such as agave, a carbonated beverage such as cola, a caffeinated beverage, a specialized flavor formulation emulating the taste of existing wines and spirits, a non-alcoholic cocktail (“mocktails”), malt beer, a dealcoholized cider, a dealcoholized wine, a dealcoholized beer, a dealcoholized spirit, tonic water and water.
  • a beverage selected from fruit juice, fruit syrup, concentrate or nectar from fruits jello, vegetable juice, a plant material such as agave, a carbonated beverage such as cola, a caffeinated beverage, a specialized flavor formulation emulating the taste of existing wines and spirits, a non-alcoholic cocktail (“mocktails”), malt beer, a dealcoholized cider, a dealcoholized wine, a dealcoholized beer, a dealcoholized spirit, tonic water and
  • the alcoholic beverage-substitute according is selected from a beer-substitute, a wine-substitute, a cider-substitute, a spirit-substitute and alcopop substitute beverage.
  • the alcoholic beverage is a beer-substitute.
  • the beer-substitute is selected from an ale-substitute, a stout-substitute, a porter-substitute, and a lager-substitute.
  • the beer-substitute comprises the compound represented by Formula I in an amount that imparts to the beverage the psychotropic effect, palatability and the pleasures of drinking provided by an alcoholic beer containing 4.8-10% alcohol by volume.
  • the beer-substitute comprises the compound represented by Formula I in an amount within a range selected from 0.20 mg/ml to 0.70 mg/ml, 0.20 to 0.68 mg/ml, 0.25 to 0.68 mg/ml, 0.28 to 0.66 mg/l, 0.30 to 0.66 mg/ml, 0.28 to 0.65 mg/ml, 0.28 to 0.60 mg/ml 0.30 to 0.60 mg/ml, 0.30 to 0.58 mg/ml, 0.30 to 0.55 mg/ml, 0.30 to 0.50 mg/ml, 0.30 to 0.48 mg/ml, 0.30 to 0.45 mg/ml, 0.30 to 0.42 mg/ml, 0.30 to 0.40 mg/ml, 0.30 to 0.38 mg/ml or 0.31 to 0.36 mg/ml.
  • the beer-substitute comprises 0.31 mg/ml to 0.33 mg/ml of the compound.
  • the beer-substitute comprises ethanol in an amount that is more than 0.01% by volume but less than 0.50%, less than 0.25%, less than 0.2%, less than 0.15%, less than 0.10%, or less than 0.05% by volume.
  • the alcoholic beverage-substitute is a wine-substitute.
  • the wine-substitute is selected from a dry red wine-substitute, a dry white wine-substitute, a semi-dry red wine-substitute, a semi-dry white wine-substitute, a rose wine-substitute, a dessert wine-substitute, a Port wine-substitute, a Champagne-substitute, a sparkling wine-substitute and vermouth-substitute.
  • the alcoholic beverage-substitute comprises the compound represented by Formula I in amount that imparts to the beverage the psychotropic effect, palatability and the pleasures of drinking provided by an alcoholic wine containing 10-14% alcohol by volume.
  • the alcoholic beverage-substitute beverage comprises the compound represented by Formula I in an amount within a range selected from 0.50 mg/ml to 1.25 mg/ml, 0.55 to 1.25 mg/ml, 0.55 to 1.20 mg/ml, 0.60 to 1.20 mg/l, 0.65 to 1.20 mg/ml, 0.70 to 1.20 mg/ml, 0.70 to 1.10 mg/ml, 0.75 to 1.10 mg/ml, 0.75 to 1.00 mg/ml, 0.78 to 1.00 mg/ml, 0.80 to 1.00 mg/ml, 0.80 to 1.05 mg/ml, 0.80 to 0.98 mg/ml or 0.80 to 0.95 mg/ml.
  • the alcoholic beverage-substitute beverage comprises 0.79 mg/ml to 0.95 mg/ml of the compound.
  • the wine-substitute comprises ethanol in an amount that is more than 0.01% by volume but less than 5.0%, less than 4.0%, less than 3.0%, less than 2.5%, less than 2.0%, less than 1.5%, less than 1.0%, less than 0.5%, less than 0.25%, less than 0.2%, less than 0.15%, less than 0.10%, or less than 0.05% by volume.
  • the alcoholic beverage substitute is a spirit-substitute.
  • the spirit-substitute is selected from a brandy-substitute, a liquor-substitute, saki-substitute, Ouzo-substitute, an arrack-substitute, a rum-substitute, a vodka-substitute, a tequila-substitute, a schnapps-substitute, a whiskey-substitute, a gin-substitute, a cordial-substitute, Cachaça-substitute and a slivovitz-substitute.
  • the alcoholic beverage-substitute comprises the compound represented by Formula I in amount that imparts to the beverage the psychotropic effect, palatability and the pleasures of drinking provided by an alcoholic spirit containing 30-40% alcohol by volume.
  • the alcoholic beverage-substituted beverage comprises the compound represented by Formula I in an amount within a range selected from 1.90 mg/ml to 2.97 mg/ml, 1.90 mg/ml to 2.64 mg/ml 1.90 mg/ml to 2.60 mg/ml, 1.90 to 2.55 mg/ml, 1.95 to 2.55 mg/ml, 1.95 to 2.50 mg/ml, 1.95 to 2.40 mg/ml, 1.95 to 2.30 mg/ml, 1.96 to 2.35 mg/l, 1.96 to 2.30 mg/ml, 1.96 to 2.28 mg/ml, 1.96 to 2.25 mg/ml, 1.96 to 2.20 mg/ml, 1.98 to 2.28 mg/ml, 1.98 to 2.25 mg/ml, or 1.98 to 2.20 mg/ml.
  • the alcoholic beverage-substituted comprises 1.98 mg/ml to 2.20 mg/ml of the compound.
  • the spirit-substitute comprises ethanol in an amount that is more than 0.01% but less than 15%, less than 14%, less than 12%, less than 11.0%, less than 10.0%, less than 9.0%, less than 8.0%, less than 7.0%, less than 6.0%, less than 4.50%, less than 4.00%, less than 3.50%, less than 3.00%, less than 2.50%, less than 2.00%, less than 1.50%, less than 1.00%, less than 0.50%, less than 0.25%, less than 0.2%, less than 0.15%, or less than 0.10%, by volume.
  • the alcoholic beverage substitute is an alcopop-substitute.
  • the alcopop-substitute is selected from a beer cooler, a wine cooler and a spirit cooler.
  • the alcoholic beverage-substitute comprises the compound represented by Formula I in amount that imparts to the beverage the psychotropic effect, palatability and the pleasures of drinking provided by an alcopop beverage containing 4.5-12.5% alcohol by volume.
  • the alcoholic beverage-substituted beverage comprises the compound represented by Formula I in an amount within a range selected from 0.25 to 0.60 mg/ml, 0.28 to 0.60 mg/l, 0.30 to 0.60 mg/ml, 0.28 to 0.58 mg/ml, 0.28 to 0.55 mg/ml 0.30 to 0.55 mg/ml, 0.30 to 0.50 mg/ml, 0.30 to 0.48 mg/ml, 0.30 to 0.45 mg/ml, 0.30 to 0.42 mg/ml, 0.30 to 0.40 mg/ml, 0.30 to 0.38 mg/ml or 0.31 to 0.36 mg/ml.
  • the alcoholic beverage-substituted comprises 0.31 mg/ml to 0.33 mg/ml of the compound.
  • the alcopop-substitute comprises ethanol in an amount that is more than 0.01% but less than 1.00%, less than 0.70%, less than 0.50%, less than 0.25%, less than 0.2%, less than 0.15%, less than 0.10%, or less than 0.05%, by volume.
  • a beer beverage comprising the beer substitute beverage as described herein and ethanol in an amount that is more than 0.5% but less than 5.00%, less than 4.50%, less than 4.00%, less than 3.50%, less than 3.00%, less than 2.50%, less than 2.00%, less than 1.50%, or less than 1.00%, by volume.
  • a wine beverage comprising the wine substitute beverage as described herein and ethanol in an amount that is more than 3.0% but less than 7.5%, less than 7.0%, less than 6.5%, less than 6.0%, less than 5.0%, less than 5.5%, less than 5.0%, less than 4.5%, less than 4.0%, or less than 3.5%, by volume.
  • a spirit beverage comprising the spirit substitute beverage as described herein and ethanol in an amount that is more than 11.0% but less than 20.0%, less than 18.0%, less than 16.0%, less than 14.0%, less than 15.0%, less than 14.0%, less than 13.5%, less than 13.0%, less than 12.5%, or less than 12.0%, by volume.
  • alcopop beverage comprising the alcopop substitute beverage as described herein and ethanol in an amount that is more than 0.5% but less than 5.00%, less than 4.50%, less than 4.00%, less than 3.50%, less than 3.00%, less than 2.50%, less than 2.00%, less than 1.50%, or less than 1.00%, by volume.
  • a beverage comprising an alcohol-free base liquid and a compound represented by Formula I as defined herein in an amount that imparts to the beverage the psychotropic effect, palatability and the pleasures of drinking provided by an alcoholic beverage having alcohol in an amount of 2% to 30% by volume.
  • the amount of the compound represented by Formula I is in the rage selected from 0.20 mg/ml to 2.97 mg/ml, 0.20 mg/ml to 0.70 mg/ml, 0.28 to 0.65 mg/ml, 0.30 to 0.60 mg/ml, 0.30 to 0.55 mg/ml, 0.30 to 0.50 mg/ml, 0.30 to 0.45 mg/ml, 0.30 to 0.40 mg/ml, 0.31 to 0.36 mg/ml, 0.50 to 1.25 mg/ml, 0.55 to 1.20 mg/ml, 0.60 to 1.20 mg/ml, 0.70 to 1.20 mg/ml, 0.70 to 1.10 mg/ml, 0.75 to 1.00 mg/ml, 0.80 to 1.00 mg/ml, 0.80 to 1.05 mg/ml, 0.80 to 0.95 mg/ml, 1.25 to 1.90 mg/ml, 1.25 to 2.00 mg/ml, 1.90 to 2.97 mg/ml, 1.90 mg/ml to
  • the beverage is selected from fruit juice, fruit syrup, concentrate or nectar from fruits, jello, vegetable juice, a plant material such as agave, a carbonated beverage such as cola, a caffeinated beverage, malt beer, tonic water and water.
  • a compound represented by Formula I as described herein in any one of the respective embodiments, for use in the manufacture of an alcoholic beverage substitute, or an alcoholic-like beverage.
  • alcoholic beverage substitute is selected from the group consisting of a beer-substitute, a wine-substitute, a spirit-substitute and an alcopop substitute.
  • a process for the preparation of an alcoholic beverage substitute comprising mixing a base liquid with a compound represented by Formula I in an amount that accounts for the psychotropic and palatability effects imparted by the alcoholic beverage.
  • the amount of the compound represented by Formula I is in the range selected from 0.20 mg/ml to 2.97 mg/ml, 0.20 mg/ml to 0.70 mg/ml, 0.28 to 0.65 mg/ml, 0.30 to 0.60 mg/ml, 0.30 to 0.55 mg/ml, 0.30 to 0.50 mg/ml, 0.30 to 0.45 mg/ml, 0.30 to 0.40 mg/ml, 0.31 to 0.36 mg/ml, 0.50 to 1.25 mg/ml, 0.55 to 1.20 mg/ml, 0.60 to 1.20 mg/ml, 0.70 to 1.20 mg/ml, 0.70 to 1.10 mg/ml, 0.75 to 1.00 mg/ml, 0.80 to 1.00 mg/ml, 0.80 to 1.05 mg/ml, 0.80 to 0.95 mg/ml, 1.25 to 1.90 mg/ml, 1.25 to 2.00 mg/ml, 1.90 to 2.97 mg/ml, 1.90 mg/ml to 2.
  • the process further comprises adding to the base liquid at least one of a flavoring agent, a colorant, an odoriferous agent, CO 2 , a viscosity modifying agent, a foaming agent, an antifoaming agent and a preservative.
  • the present invention in some embodiments thereof, relates to alcoholic beverage substitutes.
  • Alcohol is one of the favorite, commonly used, yet most dangerous psychoactive substances. People drink alcohol for several reasons, which include quenching thirst, heating or cooling the drinker, for the taste and because of the association alcoholic drinks have with other aspects of life such as food and friendship. The psychotropic effects of alcohol contribute to some of these reasons.
  • Embodiments of the present invention therefore concern the provision of drinkable substances which provide the drinker with the palatability and psychotropic effect of alcohol, and which are devoid of the adverse effects associated with alcohol consumption.
  • the drinkable substances provided herein are referred to as alcoholic-beverage substitutes, which contain a reduced or even nullified amount of alcohol.
  • Embodiments of the present invention concern drinkable substances containing one or more aminoindan derivatives, and, more particularly, 2-aminoindan derivatives, collectively represented by Formula I as presented herein, which are mostly known as dopamine D2 and/or D3 receptor ligands.
  • Mixing these compounds with liquid provides inebriating beverages that resemble, for example, beer or wine or a spirit in their user's experience.
  • These beverages although intoxicating in a way similar to alcohol (e.g., when consumed at low dosages) and even having some anxiolytic and sedative effects, are not harmful in terms of motor, cognitive and addictive effects attributed to consumption of alcoholic beverages. These beverages are therefore less toxic than commonly used ethanol-containing alcoholic beverages.
  • Exemplary embodiments of the present invention are of a beverage that is a beer substitute, obtained by mixing 125 mg of a 2-aminoindan derivative into 300 ml of a base liquid, and of a beverage that it a wine substitute, obtained by mixing this amount of the 2-aminoindan derivative into 120 ml of a base liquid.
  • each of R 1 and R 2 is independently selected from the group consisting of H, (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, (C 3 -C 8 )cycloalkyl, aryl, heteroaryl, heteroalicyclic, —O(C 1 -C 8 )alkyl, OH, —OSO 2 CF 3 , —OSO 2 —(C 1 -C 8 )alkyl, —SOR 5 , —CO 2 R 5 , —CONR 5 R 6 , —COR 5 , —CF 3 , CN, —SR 5 , —SO 2 NR 5 R 6 , —SO 2 R 5 , —OCO—(C 1 -C 8 )alkyl, —NCO—(C 1 -C 8 )alkyl, —CH 2 O—(C 1 -C 8 )al
  • each of R 3 and R 4 is independently selected from the group consisting of H, (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, (C 3 -C 8 ) cycloalkyl, and —(CH 2 ) p -thienyl, wherein p is 1, 2, 3, or 4, or alternatively, R 3 and R 4 are joined together to form a heterocylic ring (heteroalicyclic or heteroaryl) containing the nitrogen atom to which they are attached; and
  • each of R 5 and R 6 is independently selected from the group consisting of H, (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 3 -C 8 )cycloalkyl and aryl.
  • the alcoholic beverage-substitute comprises a 2-aminoindan derivative represented by Formula I as presented herein, wherein R 1 -R 6 are defined as follows:
  • each of R 1 and R 2 is independently selected from the group consisting of H, (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, (C 3 -C 8 )cycloalkyl, aryl, —OCH 3 , OH, —OSO 2 CF 3 , —OSO 2 CH 3 , —SOR 5 , —CO 2 R 5 , —CONR 5 R 6 , —COR 5 , —CF 3 , —CN, —SR 5 , —SO 2 NR 5 R 6 , —SO 2 R 5 , —CH 2 —OH, halogen, phthalimidyl, thiophenyl, pyrrolyl, pyrrolinyl, and oxazolyl, or, alternatively, R 1 and R 2 together with two or more of the phenyl carbon atoms form a —O(CH
  • R 3 and R 4 are joined together to form a heterocylic ring containing 4 to 8 carbon atoms with the nitrogen atom to which they are attached;
  • each of R 5 and R 6 is independently selected from the group consisting of H, (C 1 -C 8 ) alkyl, (C 2 -C 8 ) alkenyl, and (C 3 -C 8 ) cycloalkyl.
  • the alcoholic beverage-substitute of the invention comprises the compound represented by Formula I as described herein wherein the amino group is a secondary or tertiary amine, namely at least one of R 3 and R 4 is an alkyl, for example, propyl.
  • Secondary (or tertiary) amino groups are preferred as the 2-aminoindan derivatives containing a secondary (or tertiary) amine moiety are less susceptible to enzymatic degradation by e.g., monoamine oxidase (MAO) enzymes and are thus more potent than primary amines when acting in the brain.
  • secondary or tertiary amines are more hydrophobic and hence are more brain permeable.
  • the alcoholic beverage-substitute comprises a compound represented by Formula I, as described herein, wherein R 1 and R 2 is each independently H, —OCH 3 , or —OSO 2 CF 3 , or R 1 and R 2 together with two or more of the phenyl carbon atom form a —O(CH 2 ) m O— ring, wherein m is 1 or 2.
  • Non-limiting examples of 2-aminoindan derivatives which may be used for the preparation of the alcoholic beverage-substitutes described herein, include:
  • the 2-aminoindan derivative used is 5-methoxy-2-aminoindan (Compound 1) or 5,6-dimethoxy-2-aminoindan (Compound 2), the chemical structures of which are depicted hereinbelow.
  • each of the compounds described herein can be in a form of a pharmaceutically acceptable salt thereof.
  • the phrase “pharmaceutically acceptable salt” refers to a charged species of the parent compound and its counter-ion, which is typically used to modify the solubility characteristics of the parent compound and/or to reduce any significant irritation to an organism by the parent compound, while not abrogating the biological activity and properties of the administered compound.
  • a pharmaceutically acceptable salt of the compounds described herein may optionally be an acid addition salt comprising at least one basic (e.g., amine) group of the compound which is in a positively charged form (e.g., an ammonium ion), in combination with at least one counter-ion, derived from the selected acid, that forms a pharmaceutically acceptable salt.
  • a basic (e.g., amine) group of the compound which is in a positively charged form e.g., an ammonium ion
  • the acid addition salts of the compounds described herein may therefore be complexes formed between one or more basic groups of the drug and one or more equivalents of an acid.
  • the acid addition salts may include a variety of organic and inorganic acids, such as, but not limited to, hydrochloric acid which affords a hydrochloric acid addition salt, hydrobromic acid which affords a hydrobromic acid addition salt, acetic acid which affords an acetic acid addition salt, ascorbic acid which affords an ascorbic acid addition salt, benzenesulfonic acid which affords a besylate addition salt, camphorsulfonic acid which affords a camphorsulfonic acid addition salt, citric acid which affords a citric acid addition salt, maleic acid which affords a maleic acid addition salt, malic acid which affords a malic acid addition salt, methanesulfonic acid which affords a methanesulfonic acid (mesylate) addition salt, naphthalenesulfonic acid which affords a naphthalenesulfonic acid addition salt, oxalic acid which affords an oxalic acid addition salt,
  • a pharmaceutically acceptable salt of the compounds described herein may optionally be a base addition salt comprising at least one group of the compound which is in a form of an anion, in combination with at least one counter ion (i.e., cation) that forms a pharmaceutically acceptable salt.
  • suitable cations include metal cations of metals such as, but not limited to, sodium, potassium, magnesium, and calcium or ammonium.
  • Each of these base addition salts can be either a mono-addition salt or a poly-addition salt, as these terms are defined herein.
  • the acid or base additions salts can be either mono-addition salts or poly-addition salts.
  • addition salt refers to a salt in which the stoichiometric ratio between the counter-ion and charged form of the compound is 1:1, such that the addition salt includes one molar equivalent of the counter-ion per one molar equivalent of the compound.
  • poly-addition salt refers to a salt in which the stoichiometric ratio between the counter-ion and the charged form of the compound is greater than 1:1 and is, for example, 2:1, 3:1, 4:1 and so on, such that the addition salt includes two or more molar equivalents of the counter-ion per molar equivalent of the compound.
  • each of the compounds described herein, including the salts thereof can be in a form of a solvate or a hydrate thereof.
  • solvate refers to a complex of variable stoichiometry (e.g., di-, tri-, tetra-, penta-, hexa-, and so on), which is formed by a solute (the 2-aminoindan derivatives described herein) and a solvent, whereby the solvent does not interfere with the biological activity of the solute.
  • hydrate refers to a solvate, as defined hereinabove, where the solvent is water.
  • the present embodiments further encompass any stereoisomers (enantiomers and diastereomers) of the compounds described herein, as well as any isomorph thereof.
  • alcoholic beverage encompasses any beverage having an alcoholic content of at least 2% by volume, whether distilled, fortified, brewed, or produced by fermentation, and includes, but is not limited to, wine, beer, fermented liquids derived in whole or in part from fruit juices, such as cider and perry, spirits, flavored alcoholic beverages collectively termed herein and in the art as “alcopops”, and the like.
  • base liquid describes a liquid or a liquid form of a substance or a mixture of substances which either alone or when mixed with other additives can form a beverage.
  • the base liquid is a base beverage, namely, a liquid or a liquid form of a substance or a mixture of substances which can be used as a beverage per se, or, which, when mixed with alcohol, forms an alcoholic beverage.
  • the base beverage is an alcohol-free base beverage.
  • alcohol-free base beverage is a beverage having alcohol percentage that is no more than 50% of the alcohol content in a corresponding alcoholic beverage, preferably no more than 40%, no more than 30%, no more than 20%, no more than 15%, no more than 10%, no more than 5%, no more than 1%, no more than 0.5%, no more than 0.1%, no more than 0.05%, or no more than 0.01%, of the alcohol content acceptable for a certain beverage, including any subranges and any intermediate values there between.
  • This phrase is used herein as encompassing both base beverages that are typically used for forming alcoholic beverages, and base beverages which are typically used per se (e.g., as non-alcoholic beverages, such as juices).
  • the alcohol-free base beverage is devoid of alcohol.
  • devoid of it is meant herein less than 0.01% or less than 0.005%, or less than 0.001%, by volumes, or even null.
  • the alcoholic beverage substitutes as described herein are beverages that have residual alcohol content of 0-20% by volume, depending on the alcoholic beverage being substituted.
  • Exemplary alcohol-free base beverages which form the liquid base for the alcoholic beverage-substitutes described herein include, but are not limited to, natural or artificially flavored fruit juice (such as grape, mango, elder, apple, orange juice, and the like), vegetable juice, fruit syrup, concentrate or nectar from fruits, plant materials such as agave, jello, carbonated beverages such as cola, optionally with addition of roasted malt beer, caffeinated beverages, specialized flavor formulations emulating the taste of existing wines and spirits, non-alcoholic cocktails (“mocktails”), malt beer, dealcoholized ciders, dealcoholized wines, dealcoholized beers, dealcoholized spirits, tonic water and water.
  • natural or artificially flavored fruit juice such as grape, mango, elder, apple, orange juice, and the like
  • vegetable juice fruit syrup
  • concentrate or nectar from fruits plant materials such as agave, jello, carbonated beverages such as cola
  • plant materials such as agave, jello, carbonated beverages such as cola
  • the alcoholic beverage substitute of the invention is selected from a beer-substitute, a wine-substitute, a cider-substitute, a spirit-substitute and an alcopop-substitute beverage.
  • Typical alcoholic wine beverages include an alcoholic content of 10-14%.
  • volume % of the total volume of the beverage is meant, unless otherwise indicated.
  • beer as used herein and in the art means beverages obtained by malting and fermenting one or more of the cereal grains, and includes ale, stout, porter and lager.
  • spirit refers to distilled alcohol beverages obtained, for example, by distilling starchy material and include, but not limited to, variety of raw grain alcohols, brandies, liquors, saki, Ouzo, arrack, rum, vodka, tequila, schnapps, whiskey, gin, cordial, Cachaça, absinthe, baijiu, cau de vie, soju, aguardiente, pálinka, fernet and slivovitz.
  • the alcoholic beverage substitute is a beer-substitute.
  • Exemplary beer-substitutes include, but are not limited to, an ale-substitute, a stout-substitute, a porter-substitute, and a lager-substitute.
  • such an alcoholic beverage substitute comprises a compound represented by Formula I as described herein in an amount that imparts to the beverage the psychotropic effect, palatability and the pleasures of drinking provided by an alcoholic beer containing 4.8-10% alcohol by volume.
  • the amount of a 2-aminoindan derivative may be within a range selected from 0.20 mg/ml to 0.70 mg/ml, 0.20 to 0.68 mg/ml, 0.25 to 0.68 mg/ml, 0.28 to 0.66 mg/l, 0.30 to 0.66 mg/ml, 0.28 to 0.65 mg/ml, 0.28 to 0.60 mg/ml 0.30 to 0.60 mg/ml, 0.30 to 0.58 mg/ml, 0.30 to 0.55 mg/ml, 0.30 to 0.50 mg/ml, 0.30 to 0.48 mg/ml, 0.30 to 0.45 mg/ml, 0.30 to 0.42 mg/ml, 0.30 to 0.40 mg/ml, 0.30 to 0.38 mg/ml or 0.31 to 0.36 mg/ml, including any subranges and any intermediate values therebetween.
  • the beer-substitute beverage described herein comprises 0.31 mg/ml to 0.33 mg/ml of said compound represented by Formula I.
  • the beer substitute beverage contains ethanol in an amount that is more than 0.01% by volume but less than 0.50%, less than 0.25%, less than 0.2%, less than 0.15%, less than 0.10%, or less than 0.05% by volume, including any subranges and any intermediate values therebetween.
  • the beer-substitute is devoid of alcohol.
  • the alcoholic beverage substitute is a wine-substitute.
  • Exemplary wine-substitutes include, but are not limited to, a dry red wine-substitute, a dry white wine-substitute, a semi-dry red wine-substitute, a semi-dry white wine-substitute, a rose wine-substitute, a dessert wine-substitute, a Port wine-substitute, a Champagne-substitute, a sparkling wine-substitute and vermouth-substitute.
  • such an alcoholic beverage substitute comprises a compound represented by Formula I as described herein in amount that imparts to the beverage the psychotropic effect, palatability and the pleasures of drinking provided by an alcoholic wine containing 10-14% alcohol by volume.
  • the amount of a 2-aminoindan derivative is within a range selected from 0.50 mg/ml to 1.25 mg/ml, 0.55 to 1.25 mg/ml, 0.55 to 1.20 mg/ml, 0.60 to 1.20 mg/l, 0.65 to 1.20 mg/ml, 0.70 to 1.20 mg/ml, 0.70 to 1.10 mg/ml, 0.75 to 1.10 mg/ml, 0.75 to 1.00 mg/ml, 0.78 to 1.00 mg/ml, 0.80 to 1.00 mg/ml, 0.80 to 1.05 mg/ml, 0.80 to 0.98 mg/ml or 0.80 to 0.95 mg/ml, including any subranges and any intermediate values therebetween.
  • the wine-substitute beverage described herein comprises 0.79 mg/ml to 0.95 mg/ml of said compound represented by Formula I.
  • the wine substitute beverage contains ethanol in an amount that is more than 0.01% by volume but less than 5.0%, less than 4.0%, less than 3.0%, less than 2.5%, less than 2.0%, less than 1.5%, less than 1.0%, less than 0.5%, less than 0.25%, less than 0.2%, less than 0.15%, less than 0.10%, or less than 0.05% by volume, including any subranges and any intermediate values therebetween.
  • the wine-substitute is devoid of alcohol.
  • the alcoholic beverage substitute is a spirit-substitute.
  • Exemplary spirit-substitutes include, but are not limited to, a brandy-substitute, a liquor-substitute, saki-substitute, Ouzo-substitute, an arrack-substitute, a rum-substitute, a vodka-substitute, a tequila-substitute, a schnapps-substitute, a whiskey-substitute, a gin-substitute, a cordial-substitute, Cachaça-substitute and a slivovitz-substitute, comprising a compound represented by Formula I as described herein in an amount that imparts to the beverage the psychotropic effect, palatability and the pleasures of drinking provided by an alcoholic spirit containing 30-40% alcohol by volume.
  • the amount of a 2-aminoindan derivative is within a range selected from 1.90 mg/ml to 2.97 mg/ml, 1.90 mg/ml to 2.64 mg/ml 1.90 mg/ml to 2.60 mg/ml, 1.90 to 2.55 mg/ml, 1.95 to 2.55 mg/ml, 1.95 to 2.50 mg/ml, 1.95 to 2.40 mg/ml, 1.95 to 2.30 mg/ml, 1.96 to 2.35 mg/l, 1.96 to 2.30 mg/ml, 1.96 to 2.28 mg/ml, 1.96 to 2.25 mg/ml, 1.96 to 2.20 mg/ml, 1.98 to 2.28 mg/ml, 1.98 to 2.25 mg/ml, or 1.98 to 2.20 mg/ml, including any subranges and any intermediate values therebetween.
  • the spirit-substitute beverage described herein comprises 1.98 mg/ml to 2.20 mg/ml of said compound represented by Formula I as described herein.
  • the spirit-substitute beverage contains ethanol in an amount that is more than 0.01% but less than 15%, less than 14%, less than 12%, less than 11.0%, less than 10.0%, less than 9.0%, less than 8.0%, less than 7.0%, less than 6.0%, less than 4.50%, less than 4.00%, less than 3.50%, less than 3.00%, less than 2.50%, less than 2.00%, less than 1.50%, less than 1.00%, less than 0.50%, less than 0.25%, less than 0.2%, less than 0.15%, or less than 0.10%, by volume, including any subranges and any intermediate values therebetween.
  • the spirit-substitute is an alcohol-free beverage as defined herein.
  • the alcoholic beverage substitute is an alcopop-substitute.
  • Alcopop beverages also termed herein and in the art “coolers” or “spirit coolers”, are flavored alcoholic beverages or flavored malt beverages based on fruit juice or nectar, and/or a variety of naturally and/or artificially flavored syrups.
  • Exemplary alcopop beverages include, but are not limited to (i) a malt beverage, designate herein “a beer cooler”, containing a malt base or beer and at least 5% by volume of added natural or artificial blending material, such as fruit juice, flavors, flavorings, colorings, and, optionally, preservatives; (ii) a wine cooler which is a beverage containing wine and more than 15% by volume of added natural or artificial blending material, such as fruit juices, flavors, flavorings, adjuncts, water (plain, carbonated, or sparkling), colorings, and, optionally, preservatives; and (iii) a beverage designated herein “a spirit cooler”, containing distilled alcohol, and added natural or artificial blending material, such as fruit juices, flavors, flavorings, colorings, and, optionally, preservatives.
  • a malt beverage designate herein “a beer cooler”, containing a malt base or beer and at least 5% by volume of added natural or artificial blending material, such as fruit juice, flavors,
  • Alcopop brands are numerous and their alcoholic base varies greatly. Most alcopop beverages contain 4-7% alcohol by volume, and some may even contain as much as 12.5% alcohol by volume. Some notable brands include, but are not limited to, Smirnoff Ice, Mike's Hard Lemonade, Bacardi Breezer, Skyy Blue, Jack Daniel's Hard Cola, WKD Original Vodka, Six Degrees and MG Spirits.
  • such an alcoholic beverage substitute comprises a compound represented by Formula I as described herein in an amount that imparts to the beverage the psychotropic effect, palatability and the pleasures of drinking provided by an alcoholic alcopop containing 4-7% alcohol by volume.
  • the amount of a 2-aminoindan derivative may be within a range selected from 0.25 to 0.60 mg/ml, 0.28 to 0.60 mg/l, 0.30 to 0.60 mg/ml, 0.28 to 0.58 mg/ml, 0.28 to 0.55 mg/ml 0.30 to 0.55 mg/ml, 0.30 to 0.50 mg/ml, 0.30 to 0.48 mg/ml, 0.30 to 0.45 mg/ml, 0.30 to 0.42 mg/ml, 0.30 to 0.40 mg/ml, 0.30 to 0.38 mg/ml or 0.31 to 0.36 mg/ml, including any subranges and any intermediate values therebetween.
  • the alcopop-substitute beverage described herein comprises 0.31 mg/ml to 0.33 mg/ml of said compound represented by Formula I.
  • the alcopop substitute beverage contains ethanol in an amount that is more than 0.01% by volume but less than 1.00%, less than 0.70%, less than 0.50%, less than 0.25%, less than 0.2%, less than 0.15%, less than 0.10%, or less than 0.05% by volume, including any subranges and any intermediate values therebetween.
  • the alcopop-substitute is completely devoid of alcohol.
  • the alcoholic beverage substitute optionally contains alcohol (ethanol), yet in an amount that is no more than 50% of the ethanol content acceptable for a certain kind of a corresponding alcoholic beverage (the alcoholic beverage that is intended to be substituted).
  • the beverage is an alcohol-reduced beverage.
  • the alcohol-reduced beverage contains alcohol in an amount of 20-50%, 20-40%, 20-30%, or 30-40% of the amount of alcohol in a corresponding alcoholic beverage.
  • the alcohol-reduced beverage is selected from an alcohol-reduced spirit, having alcohol content of about 11% to about 20% by volume, an alcohol-reduced wine beverage that has a reduced alcohol content of about 3% to about 7.5% by volume, an alcohol-reduced beer beverage that has a reduced alcohol content of about 0.5% to about 2.5% by volume or about 2.5% to about 5.0% by volume, or an alcohol-reduced alcopop beverage that has a reduced alcohol content of about 0.5% to about 2.5% or 2.5% to about 5.0% by volume.
  • the alcohol-reduced beer beverage contains ethanol in an amount that is more than 0.5% but less than 5.00%, less than 4.50%, less than 4.00%, less than 3.50%, less than 3.00%, less than 2.50%, less than 2.00%, less than 1.50%, or less than 1.00%, by volume, including any subranges and any intermediate values therebetween.
  • the alcohol-reduced wine beverage contains ethanol in an amount that is more than 3.0% but less than 7.0%, less than 6.5%, less than 6.0%, less than 5.0%, less than 5.5%, less than 5.0%, less than 4.5%, less than 4.0%, or less than 3.5%, by volume, including any subranges and any intermediate values there between.
  • the alcohol-reduced spirit beverage contains ethanol in an amount that is more than 11.0% but less than 20.0%, less than 18.0%, less than 16.0%, less than 14.0%, less than 15.0%, less than 14.0%, less than 13.5%, less than 13.505%, less than 12.5%, or less than 12.0%, by volume, including any subranges and any intermediate values therebetween.
  • the alcohol-reduced alcopop beverage contains ethanol in an amount that is more than 0.5% but less than 5.00%, less than 4.50%, less than 4.00%, less than 3.50%, less than 3.00%, less than 2.50%, less than 2.00%, less than 1.50%, or less than 1.00%, by volume, including any subranges and any intermediate values there between.
  • the base liquid or base beverage is formulated to include additives, such as flavoring agents, colorants, odoriferous agents, CO 2 and/or other additives such as viscosity modifying agents, foaming agents, antifoaming agents, and preservatives that account for the taste and texture of wine or beer or spirit, such that the substitute beverage will contain at least part or all the ingredients used to form the corresponding alcoholic beverages, except for the alcohol content therein.
  • additives used in the alcohol-substitute and alcohol reduced beverages described herein are FDA-approved, and/or edible.
  • the additives are selected as soluble in the base beverage or base liquid.
  • flavoring agent and “odoriferous agent”, as used herein, describe a class of substances which are added to edible products in order to induce a certain flavor or smell in the product, and are commonly referred to also as “flavorants”. Flavorants can be synthetic or natural extracts, which are extracted from a source substance. Typical flavorants are specific and often complex mixtures of singular naturally occurring or synthetic flavor compounds combined together to either imitate or enhance a natural flavor.
  • esters which can be characterized by a typical flavor, such as, for some non-limiting examples, diacetyl which gives a buttery flavor, isoamyl acetate that is perceived as banana, cinnamic aldehyde which is the basis for the typical flavor of cinnamon, ethyl propionate is perceived as fruity, limonene is perceived as orange, ethyl-(E, Z)-2,4-decadienoate is perceived as pear, allyl hexanoate is perceived as pineapple, ethyl maltol, is perceived as sugar or cotton candy, methyl salicylate is known as the wintergreen flavor, and benzaldehyde is perceived as bitter almond.
  • diacetyl which gives a buttery flavor
  • isoamyl acetate that is perceived as banana
  • cinnamic aldehyde which is the basis for the typical flavor of cinnamon
  • ethyl propionate is perceived as fruity
  • the flavoring agent used is of a natural source and can be, for example, an extract of a fruit, a vegetable, a herb or of any other edible substance, a fruit juice or a vegetable juice, or any combination thereof.
  • Such natural flavoring agents are often considered also as providing an added nutritional value to an alcohol-substitute beverage containing same.
  • colorant refers to any natural or synthetic coloring substance, and describes any substance that is added to food or drink in order to alter its color.
  • exemplary usable colorants include, but are not limited to, synthetic colorants such as FD&C Blue No. 1—Brilliant Blue FCF (E133), FD&C Blue No. 2—Indigotine (E132), FD&C Green No. 3—Fast Green FCF (E143), FD&C Red No. 40—Allura Red AC (E129), FD&C Red No. 3—erythrosine (E127), FD&C Yellow No. 5—tartrazine (E102), and FD&C Yellow No.
  • synthetic colorants such as FD&C Blue No. 1—Brilliant Blue FCF (E133), FD&C Blue No. 2—Indigotine (E132), FD&C Green No. 3—Fast Green FCF (E143), FD&C Red No. 40—Allura Red AC (E129), FD&C Red No
  • preservative describes a synthetic or natural additive substance that is added to edible products in order to prevent or retard chemical and biochemical decomposition of the product by oxygen, moisture and/or microbes.
  • exemplary anti-microbial preservatives include, but are not limited to, calcium propionate, sodium nitrate, sodium nitrite, sulfites (sulfur dioxide, sodium bisulfite, potassium hydrogen sulfite, etc.) and disodium EDTA, sodium benzoate, potassium sorbate.
  • Natural substances that retard microorganisms growth include lactic acid, salt, sugar and vinegar.
  • antioxidant preservatives include, but are not limited to, butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT).
  • Natural antioxidants include, but are not limited to, herbal extracts such as rosemary and oregano, and vitamins such as Vitamin E and Vitamin C (ascorbic acid)
  • foaming agent describes an edible surfactant, which when present in small amounts, facilitates the formation of a foam, or enhances its colloidal stability by inhibiting the coalescence of bubbles.
  • foaming agents include, without limitation, sodium laureth/lauryl sulfate (SLS), sodium lauryl ether sulfate (SLES) and ammonium lauryl sulfate (ALS).
  • antifoaming agent describes an edible substance that inhibits the formation of foam and curbs effusion or effervescence in edible products.
  • An exemplary antifoaming agent is polydimethylsiloxane.
  • viscosity modifying agent or “thickener” as used herein are interchangeable and describe agents that enables to control the viscosity of the beverages described herein.
  • thickeners include, but are not limited to, starch-based thickeners such as maltodextrin and gum-based thickeners such as xanthan or cellulose gum.
  • natural or artificial flavourings and taste-improving additives may be added to the alcoholic beverage substitutes described herein.
  • Non-limiting examples include fruit flavours, preferably natural flavours, such as elder, grape, orange, ginger, red apple or lemon grass.
  • Artificial or synthetic flavourings include, but are not limited to, cola flavours, ice cream flavors, anise flavor, amaretto flavor. These additives are added in addition to or instead of those found in the alcoholic beverage, if indeed present therein.
  • any one of the alcohol-free base beverages described herein is made an “alcoholic-like” beverage in terms of the psychotropic effect it imparts, e.g., intoxication, palatability and the pleasures of drinking, by mixing the base beverage with an amount of a 2-aminoindan derivative, as described herein, that would account for alcohol (corresponds in its effect to an effect of) in an amount of 2% to 30% or more, for example, 2%, 3%, 5%, 8%, 10%, 12%, 15%, 18%, 20%, 30%, or more.
  • the amount of a compound represented by Formula I as described herein, added to the base beverage is in the range selected from 0.20 mg/ml to 2.97 mg/ml, 0.20 mg/ml to 0.70 mg/ml, 0.28 to 0.65 mg/ml, 0.30 to 0.60 mg/ml, 0.30 to 0.55 mg/ml, 0.30 to 0.50 mg/ml, 0.30 to 0.45 mg/ml, 0.30 to 0.40 mg/ml, 0.31 to 0.36 mg/ml, 0.50 to 1.25 mg/ml, 0.55 to 1.20 mg/ml, 0.60 to 1.20 mg/ml, 0.70 to 1.20 mg/ml, 0.70 to 1.10 mg/ml, 0.75 to 1.00 mg/ml, 0.80 to 1.00 mg/ml, 0.80 to 1.05 mg/ml, 0.80 to 0.95 mg/ml, 1.25 to 1.90 mg/ml, 1.25 to 2.00 mg/ml, 1.90 to 2.97 mg/ml, 1.90 mg/m
  • Exemplary alcohol-free base beverages that can be made into alcohol-like beverages by addition of a compound represented by Formula I as described herein include, but are not limited to, fruit juice, fruit syrup, concentrate or nectar from fruits, jello, vegetable juice, plant materials such as agave, carbonated beverages such as cola, caffeinated beverages, malt beer, tonic water and water.
  • Alcopop substitutes for example, are made by adding the aminoindan derivative to fruit juices containing flavors, flavorings, colorings, and, optionally, preservatives, etc., instead of the alcoholic component.
  • the alcoholic beverage substitute may be obtained from a dealcoholized beverage such as beer or wine or even a distilled alcoholic (spirit) beverage, which were dealcoholized using any of the methods known in the art, for example boiling as taught in U.S. Pat. No. 1,390,710, or using heated steam as taught in U.S. Pat. No. 1,256,894, or using porous, hydrophobic solid (such as zeolite or a monolithic microporous solid) to specifically adsorb ethanol, as taught in U.S. Pat. No. 6,472,009. Reconstituted dealcoholized beverages retain as much as possible of the original drinking experience.
  • a dealcoholized beverage such as beer or wine or even a distilled alcoholic (spirit) beverage
  • an aminoindan derivative compound represented by Formula I as described herein is added to the dealcoholized beverage in an amount that corresponds to the original alcohol percentage of the alcoholic beverage, along with flavor- and sense-essential elements that replace the original elements in the alcoholic beverage which were removed or reduced in the dealcoholization process.
  • Such added ingredients include, for example, small quantities of volatile acids, such as formic acid, acetic acid and propionic acid, which replace the naturally contained volatile acids of the beverages removed or destroyed, e.g., due to boiling in a dealcoholization process, as described, for example in U.S. Pat. No. 1,401,700.
  • volatile acids such as formic acid, acetic acid and propionic acid
  • a small proportion of volatile acid or a mixture of volatile acids is added to the cooled dealcoholized beverage.
  • the proportion of volatile acetic acid that may be added is approximately 12.3 mg per 100 ml of dealcoholized beer, or in the case of formic, propionic and butyric acids or mixtures thereof with or without acetic acid, the equivalent of this quantity, provided that the amount of volatile acid added does not exceeds 0.05% by weight. It is assumed that the addition of the volatile acids in the amounts described herein has a marked preserving effect upon the beverage, similar to that produced by the alcohol in natural alcoholic fermented beverages.
  • the beverage may be perfected as described, for example, in U.S. Pat. No. 1,302,551, by adding fermentable matter and live yeast, for example, fermenting wort in the case of dealcoholized beer, and causing fermentation to proceed without carbonating the beverage, thereby promoting yeast propagation.
  • the volatile acid may be added after the yeast fermentation has been completed and before artificial carbonation.
  • tryptophan and cliousclatine that act as psychotropic agents that give individuals the pleasures of drinking wine, may be added.
  • the palatability, and particularly the “smoothness” of some alcoholic-substitute beverages described herein, particularly non-alcoholic substitutes of whiskies, brandies, cordials, liqueurs, and especially gins, may be improved by the addition of polyhydric alcohols having three or more hydroxyl groups.
  • polyhydric alcohols having three or more hydroxyl groups such as sorbitol, are added to impart the desired smoothness to the non-alcoholic beverage substitute.
  • a technical sorbitol which is produced by the reduction of glucose and which contains, in addition to sorbitol, moisture, other polyhydric alcohols, small amounts of ash, sugar, organic acids, and other impurities, is added so as to significantly improve the palatability and smoothness of the spirit-substitute beverage.
  • Other polyhydric alcohols having more than three hydroxyl groups that are used in some embodiments of the present invention, either alone or mixed with sorbitol and/or glycerine are mannitol, iditol and galactitol (dulcitol), or any mixtures thereof or any mixtures of these with any other desired substances used as modifiers or diluents, or otherwise improve the finished product.
  • sorbitol is added to a wine-substitute beverage of the invention, in amounts higher than its normal content in alcoholic wine for the purpose of improving palatability of the beverage.
  • salts of glycine and alanine are used for improving the smoothness, mellowness and flavor of wine or spirit substitutes.
  • Addition of 0.01-6.0% (w/v) of citrate, tartrate and cyclamate salts of glycine and alanine is known to imitate the effect of long aging of wines and whiskies, as taught, for example in U.S. Pat. No. 3,558,325.
  • the volatile acid, fermentable matter and live yeast, tryptophan, cliousclatine or polyhydric alcohols it is preferred that the latter be stored for a 0.5-3 months period at a low temperature, since under these conditions an improvement in the flavor, taste and bouquet of the beverage takes place, apparently by an esterifying action of the volatile acids in the presence of the various enzymes contained in the beverage, particularly when perfected by a secondary yeast propagation.
  • a suitable period of time for example, in the case of dealcoholized beer, two weeks at a temperature of 10 to 15° C., the esterifying or aging action will have been carried to a sufficient extent and the beverage may be prepared for the market.
  • the alcoholic beverage-substitutes described herein may be contained in any of the known containers applied for alcoholic drinks or beverages in general, for example, a 330 ml, 500 ml, 750 ml and 1 liter bottle or tin, or in a barrel.
  • the stability of the alcoholic beverage substitute obtained according to any of the embodiments of the present invention is preferably more than 365 days at room temperature, and it may be stored for up to 999 days at 10° C.
  • a process for the preparation of an alcoholic beverage substitute comprises mixing an alcohol-free base beverage as defined herein with an amount of a compound represented by Formula I as described herein that accounts for the psychotropic and palatability effects imparted by an alcoholic beverage.
  • the alcoholic beverage substitute is a beer-substitute, a wine-substitute, a spirit substitute, cider-substitute or an alcopop substitute as described herein.
  • the process described herein is for the preparation of an alcohol-reduced beverage as described herein.
  • an alcoholic-like beverage is produced by mixing an alcohol-free base beverage as described herein with an amount of a compound represented by Formula I as described herein that accounts for the psychotropic and palatability effects imparted by alcohol in the amount of 2% to 30% by volume.
  • base liquid and “beverage” is intended to include all such new technologies a priori.
  • a numerical range is indicated herein, it is meant to include any cited numeral (fractional or integral) within the indicated range.
  • the phrases “ranging/ranges between” a first indicate number and a second indicate number and “ranging/ranges from” a first indicate number “to” a second indicate number are used herein interchangeably and are meant to include the first and second indicated numbers and all the fractional and integral numerals therebetween.
  • compositions, method or microcapsules may include additional ingredients, steps and/or parts, but only if the additional ingredients, steps and/or parts do not materially alter the basic and novel characteristics of the claimed composition, method or structure.
  • a compound or “at least one compound” may include a plurality of compounds, including mixtures thereof.
  • method refers to manners, means, techniques and procedures for accomplishing a given task including, but not limited to, those manners, means, techniques and procedures either known to, or readily developed from known manners, means, techniques and procedures by practitioners of the chemical, pharmacological, biological, biochemical and medical arts.
  • alkyl refers to a saturated aliphatic hydrocarbon including straight chain and branched chain groups.
  • the alkyl group has 1 to 20 carbon atoms. Whenever a numerical range; e.g., “1-20”, is stated herein, it implies that the group, in this case the alkyl group, may contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, etc., up to and including 20 carbon atoms. More preferably, the alkyl is a medium size alkyl having 1 to 10 or 1 to 8 carbon atoms. Most preferably, unless otherwise indicated, the alkyl is a lower alkyl having 1 to 8 carbon atoms.
  • alkenyl refers to a partially unsaturated hydrocarbon including straight chain and branched chain groups, which consists of at least two carbon atoms and at least one carbon-carbon double bond.
  • the alkenyl is a medium size alkenyl having 2 to 10 or 2 to 8 carbon atoms. Most preferably, unless otherwise indicated, the alkenyl is a lower alkenyl having 2 to 4 carbon atoms.
  • Non-limiting examples of alkenyl include ethenyl (vinyl), propenyl, butenyl, pentenyl and hexenyl.
  • alkynyl refers to an a partially unsaturated hydrocarbon including straight chain and branched chain groups, which consists of at least two carbon atoms and at least one carbon-carbon triple bond.
  • the alkynyl is a medium size alkynyl having 2 to 10 or 2 to 8 carbon atoms. Most preferably, unless otherwise indicated, the alkynyl is a lower alkynyl having 2 to 8 carbon atoms.
  • Non-limiting examples of alkynyl include ethynyl, propynyl, butynyl, pentynyl and hexynyl.
  • a “cycloalkyl” group refers to a saturated, all-carbon monocyclic or polycyclic (fused ring, i.e., rings which share an adjacent pair of carbon atoms) group, having 3 to 20, preferably 3 to 8 carbon atoms.
  • Examples, without limitation, of cycloalkyl groups are cyclopropane, cyclobutane, cyclopentane, cyclohexane and cycloheptane.
  • aryl group refers to an all-carbon monocyclic or polycyclic (fused-ring i.e., rings which share adjacent pairs of carbon atoms) groups having a completely conjugated pi-electron system. Examples, without limitation, of aryl groups are phenyl, naphthalenyl and anthracenyl.
  • heteroaryl group refers to a monocyclic or polycyclic (fused ring, i.e., rings which share an adjacent pair of atoms) group having in the ring(s) one or more heteroatoms, selected from nitrogen, oxygen and sulfur and, in addition, having a completely conjugated pi-electron system.
  • heteroaryl groups include pyrrole, furan, thiophene, imidazole, oxazole, thiazole, pyrazole, pyridine, pyrimidine, quinoline, isoquinoline, phthalimide, and purine.
  • a “heteroalicyclic” group as used herein refers to a monocyclic or polycylic (namely, a fused ring group as defined herein) having in the ring(s) one or more atoms such as nitrogen, oxygen and sulfur.
  • the rings may also have one or more double bonds. However, the rings do not have a completely conjugated pi-electron system.
  • Representative examples are piperidine, piperazine, tetrahydro furane, tetrahydropyrane, morpholine, pyrroline and the like.
  • hydroxyalkyl refers to an alkyl, as this term is defined herein, substituted by an OH group, and includes, for example, hydroxymethyl, hydroxyethyl, hydroxypropyl and hydroxy-n-butyl.
  • thienyl refers to the radical:
  • halogen which is also referred to herein interchangeably as “halo”, includes chloro (Cl), bromo (Br), iodo (I) and fluoro (F).
  • any of the alkyl, alkenyl, alkynyl, cycloalkyl, heteroaryl, heteroclicylic or aryl group as defined herein may be substituted or unsubstituted.
  • the substituent group can be, for example, alkyl, —O—(C 1 -C 8 )alkyl, —O—(C 3 -C 8 )cycloalkyl, trihaloalkyl, hydroxyalkyl, (C 3 -C 8 ) cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, heteroalicyclic, halo, OH, O-aryl, —SH, —S—(C 1 -C 8 )alkyl, —S—(C 3 -C 8 )cycloalkyl, —S-aryl, —O—S ⁇ O, —S( ⁇ O) 2 —R′, —CN, —NO 2 , —O

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US20210330609A1 (en) * 2014-12-09 2021-10-28 Ezekiel Golan Binge behavior regulators

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